"Highwayman" is a song written by American songwriter Jimmy Webb, about a soul with incarnations in four different places in time and history, a highwayman, a sailor, a construction worker on the Hoover Dam, and finally as a starship captain.[1]


 [hide*1 Background


Webb wrote the song while in a London hotel suite. His suite included a piano, and after he woke up from a dream about being an English highwayman, he went to the piano and started writing the song.[2]

"I had a black cape and pistols, and I was definitely a bandit. A highwayman, as it were. I was being chased within an inch of my life by these grenadiers on horseback, and I knew for a fact that if they caught me, they were going to kill me."

— Jimmy Webb, on the song: "The Highwayman".[3]

Webb's lyrics allude to the life of hanged highwayman Jonathan Wild,[4] the "sailer's graveyard" near Cape Horn, and the deaths of over 100 men during the Hoover Dam construction near Boulder City, Nevada.

He first recorded it for his 1977 album El Mirage, released that May.

Glen Campbell version[edit]Edit

Webb then brought the song to Glen Campbell, who recorded it in 1978. But his record label, Capitol Records, wanted him to go in a different direction and record music like the group The Knack.[5] Campbell wanted to release the song as a single, but Capitol refused.[6] After recording 30 albums for the only record label he had worked with since 1962, Campbell got up and left the main studios of Capitol, never to return. Although he would record three more albums with Capitol, the relationship was at an end.[7] After disagreeing with the label, he released the song on his 1979 album Highwayman, released in October.

The Highwaymen version[edit]Edit

Single by The Highwaymen
from the album Highwayman
Released May 6, 1985
Recorded 1984
Genre Country
Length 3:06
Label Columbia
Writer(s) Jimmy Webb
Producer(s) Chips Moman
The Highwaymen singles chronology


"Desperados Waiting for a Train"


Campbell then played the song for Johnny Cash. Webb brought the song to Waylon Jennings in about 1981, but Jennings, having heard the Campbell version, said "I just couldn't see it then".[1] Cash, Jennings, Willie Nelson and Kris Kristofferson were all together in Switzerland doing a television special and decided that they should do a project together.[8] In 1984, while the four were recording, Marty Stuart again played the song for Johnny Cash, saying that it would be perfect for them, four verses, four souls, and four of them.[9] Campbell then played the song to all four of them, and the quartet had the name for their new supergroupThe Highwaymen, the name of their first album, Highwayman, and the name of their first single. The four thought it was a perfect name for them because they were always on the road and all four had the image of being outlaws in country music.[8] In their version of the song, each of the four verses was sung by a different singer: first Nelson, then Kristofferson, Jennings, and finally Cash. Their cover of the Webb song remains the most popular and widely known of The Highwaymen's songs, being their only song to reach number 1 ("Desperados Waiting for a Train" at number 15 is the next closest).[10] The version by the quartet entered the Hot Country Songs Billboard chart on May 18, 1985, rose to number 1, and spent 20 weeks total on the chart.[11] It finished 1985 as the number 5 country song of the year in terms of airplay.[12]

Chart positions[edit]Edit

Chart (1985) Peak


U.S. Billboard Hot Country Singles 1
Canadian RPM Country Tracks 1
Canadian RPM Adult Contemporary Tracks 19
Preceded by

"I'm for Love" by Hank Williams, Jr.

Billboard Hot Country Singles

number-one single August 17, 1985

Succeeded by

"Real Love" by Dolly Parton and Kenny Rogers

Preceded by

"40 Hour Week (For a Livin')" by Alabama

RPM Country Tracks

number-one single August 24, 1985


The version by The Highwaymen earned songwriter Jimmy Webb a Grammy Award for 1985's "Best Country Song".[13]

Other Versions[edit]Edit

Heavy metal band Iced Earth covered Highwayman on their 2014 album, Plagues of Babylon.

Finnish rock musician Pate Mustajärvi recorded a Finnish-language version of the song for his album Ukkometso released in 2000.

Independent Americana/folk artist Jake Smith aka The White Buffalo covered Highwayman as "The Highwayman" and recorded his version in 2013.

Arbouretum covered the song on their 2011 album, "The Gathering".

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